Co-reporter:Juan Zhao, Zijun Wang, Run Wang, Zhenguo Chi, Junsheng Yu
Journal of Luminescence 2017 Volume 184() pp:287-292
Publication Date(Web):April 2017
DOI:10.1016/j.jlumin.2016.11.067
Hybrid white organic light-emitting devices (OLEDs) are fabricated by employing non-doped emitting layers (EMLs), which are consisted of a blue thermally activated delayed fluorescent (TADF) emitter 9,9-dimethyl-9,10-dihydroacridine-diphenylsulfone (DMAC-DPS) and an ultrathin yellow iridium complex bis[2-(4-tertbutylphenyl)benzothiazolato-N,C2′] iridium (acetylacetonate) [(tbt)2Ir(acac)]. With thickness optimization of DMAC-DPS, a white OLED achieves maximum current efficiency, power efficiency and external quantum efficiency of 34.9 cd/A, 29.2 lm/W and 11.4%, respectively, as well as warm white emission with relatively stable electroluminescence spectra. The results suggest that, bipolar charge carrier transport property and concentration independent property of DMAC-DPS, charge carrier trapping effect of the ultrathin (tbt)2Ir(acac), and balanced self-emission process and energy transfer process between DMAC-DPS and (tbt)2Ir(acac), contribute to high device performance.
Co-reporter:Zhiyong Yang;Zhu Mao;Zongliang Xie;Yi Zhang;Siwei Liu;Juan Zhao;Jiarui Xu;Matthew P. Aldred
Chemical Society Reviews 2017 vol. 46(Issue 3) pp:915-1016
Publication Date(Web):2017/02/06
DOI:10.1039/C6CS00368K
Organic materials that exhibit thermally activated delayed fluorescence (TADF) are an attractive class of functional materials that have witnessed a booming development in recent years. Since Adachi et al. reported high-performance TADF-OLED devices in 2012, there have been many reports regarding the design and synthesis of new TADF luminogens, which have various molecular structures and are used for different applications. In this review, we summarize and discuss the latest progress concerning this rapidly developing research field, in which the majority of the reported TADF systems are discussed, along with their derived structure–property relationships, TADF mechanisms and applications. We hope that such a review provides a clear outlook of these novel functional materials for a broad range of scientists within different disciplinary areas and attracts more researchers to devote themselves to this interesting research field.
Co-reporter:Zhiyong Yang;Zhu Mao;Zongliang Xie;Yi Zhang;Siwei Liu;Juan Zhao;Jiarui Xu;Matthew P. Aldred
Chemical Society Reviews 2017 vol. 46(Issue 3) pp:915-1016
Publication Date(Web):2017/02/06
DOI:10.1039/C6CS00368K
Organic materials that exhibit thermally activated delayed fluorescence (TADF) are an attractive class of functional materials that have witnessed a booming development in recent years. Since Adachi et al. reported high-performance TADF-OLED devices in 2012, there have been many reports regarding the design and synthesis of new TADF luminogens, which have various molecular structures and are used for different applications. In this review, we summarize and discuss the latest progress concerning this rapidly developing research field, in which the majority of the reported TADF systems are discussed, along with their derived structure–property relationships, TADF mechanisms and applications. We hope that such a review provides a clear outlook of these novel functional materials for a broad range of scientists within different disciplinary areas and attracts more researchers to devote themselves to this interesting research field.
Co-reporter:Tao Yu;Depei Ou;Leyu Wang;Shizhao Zheng;Zhiyong Yang;Yi Zhang;Siwei Liu;Jiarui Xu;Matthew P. Aldred
Materials Chemistry Frontiers 2017 vol. 1(Issue 9) pp:1900-1904
Publication Date(Web):2017/08/23
DOI:10.1039/C7QM00160F
A carbazole containing triphenylethylene derivative (TrPEBCar) has been designed and synthesized, which combines aggregation-induced emission (AIE), piezochromism and photochromism together. In the crystalline state, an intensive emission band at 448 nm was detected. After pressing the crystalline solid, a [crystalline–amorphous] morphological transition takes place, in which the resulting amorphous state of TrPEBCar exhibits a different color and a red-shifted emission band at 470 nm. Photochromic behavior of TrPEBCar is achieved by utilizing a stilbene-type intramolecular photocyclization in the crystalline state. In addition, we report for the first time morphology-dependent photochromism, in which the photochromic properties of TrPEBCar are only observed in the crystalline state but not in the amorphous state. Therefore, the methods of pressing/fuming and heating/fuming act as gates to switch the photochromic properties by changing the aggregation states between the crystalline and amorphous states. By combining the piezochromic properties with the photochromic properties, the ON/OFF states of TrPEBCar can easily be observed by the different colors and emission properties. The triphenylethylene derivative with simple molecular structure provides a new approach for gated photochromic materials with both switch and indicator.
Co-reporter:Tao Yu;Depei Ou;Leyu Wang;Shizhao Zheng;Zhiyong Yang;Yi Zhang;Siwei Liu;Jiarui Xu;Matthew P. Aldred
Materials Chemistry Frontiers 2017 vol. 1(Issue 9) pp:1900-1904
Publication Date(Web):2017/08/23
DOI:10.1039/C7QM00160F
A carbazole containing triphenylethylene derivative (TrPEBCar) has been designed and synthesized, which combines aggregation-induced emission (AIE), piezochromism and photochromism together. In the crystalline state, an intensive emission band at 448 nm was detected. After pressing the crystalline solid, a [crystalline–amorphous] morphological transition takes place, in which the resulting amorphous state of TrPEBCar exhibits a different color and a red-shifted emission band at 470 nm. Photochromic behavior of TrPEBCar is achieved by utilizing a stilbene-type intramolecular photocyclization in the crystalline state. In addition, we report for the first time morphology-dependent photochromism, in which the photochromic properties of TrPEBCar are only observed in the crystalline state but not in the amorphous state. Therefore, the methods of pressing/fuming and heating/fuming act as gates to switch the photochromic properties by changing the aggregation states between the crystalline and amorphous states. By combining the piezochromic properties with the photochromic properties, the ON/OFF states of TrPEBCar can easily be observed by the different colors and emission properties. The triphenylethylene derivative with simple molecular structure provides a new approach for gated photochromic materials with both switch and indicator.
Co-reporter:Jun-ru Chen;Juan Zhao;Bing-jia Xu
Chinese Journal of Polymer Science 2017 Volume 35( Issue 2) pp:282-292
Publication Date(Web):2017 February
DOI:10.1007/s10118-017-1894-9
A polymer (poly(9,10-anthracenevinylene-alt-4,4'-(9,9-bis(4-(4'-(1,2,2'-triphenylvinyl)phenoxy)butyl)-9H-fluorene-2,7-diyl) dibenzaldehyde), P1 was successfully synthesized through the Wittig-Horner reaction by employing fluorene and 9,10-distyrylanthracene moieties as building blocks for backbone and tetraphenylethenes as pendant groups. Photophysical and thermal properties of the resulting polymeric emitter were fully characterized by ultraviolet-visible (UV-Vis) absorption and photoluminescence (PL) spectra, thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). While P1 emits an orange-light centered at 567 nm in dilute tetrahydrofuran (THF) solution, the solid powder of the polymer exhibits strong yellow emission peaked at 541 nm. It is also found that the as-synthesized polymer shows unique property of aggregation-enhanced emission (AEE). In addition, P1 possesses high thermal stability with a decomposition temperature (Td,5% of 430 °C and high morphological stability with a glass transition temperature (Tg of 171 °C. Under the stimulus of mechanical force, the emission of P1 can be changed from yellow to red (Δλmax = 61 nm), showing a remarkable mechanochromism. The results from XRD analysis suggest that such mechanochromic phenomenonof P1 is probably caused by the destruction of crystalline structure, which leads to the conformational planarization of the distyrylanthracene moieties forming by the polymerization and the increase of molecular conjugation of the backbone.
Co-reporter:Tao Yu;Depei Ou;Zhiyong Yang;Qiuyi Huang;Zhu Mao;Junru Chen;Yi Zhang;Siwei Liu;Jiarui Xu;Martin R. Bryce
Chemical Science (2010-Present) 2017 vol. 8(Issue 2) pp:1163-1168
Publication Date(Web):2017/01/30
DOI:10.1039/C6SC03177C
This study probes the effect of intramolecular rotations on aggregation-induced emission (AIE) and leads to a kind of supramolecular mechanoluminescent material. Two hydrogen-bonded organic frameworks (HOFs), namely HOFTPE3N and HOFTPE4N, have been constructed from nitro-substituted tetraphenylethene (TPE) building blocks, namely tris(4-nitrophenyl)phenylethene (TPE3N) and tetrakis(4-nitrophenyl)ethene (TPE4N). Using single-crystal X-ray diffraction analysis, two types of pores are observed in the HOFTPE4N supramolecular structure. The pore sizes are 5.855 Å × 5.855 Å (α pores) and 7.218 Å × 7.218 Å (β pores). Powder X-ray diffraction and differential scanning calorimetry studies further reveal that the α pores, which contain nitrophenyl rings, quench the emission of HOFTPE4N. This emission can be turned on by breaking the α pores in the HOFs by grinding the sample. Temperature-dependent emission studies demonstrate that the emission quenching of HOFTPE4N is attributed to the intramolecular rotations of nitro-substituted phenyl units within the space of the α pores. These results clearly reveal AIE by controlling the intramolecular rotations, which can serve as a basis for developing mechanoluminescent materials.
Co-reporter:Zongliang Xie;Qiuyi Huang;Tao Yu;Leyu Wang;Zhu Mao;Wenlang Li;Zhan Yang;Yi Zhang;Siwei Liu;Jiarui Xu;Matthew P. Aldred
Advanced Functional Materials 2017 Volume 27(Issue 47) pp:
Publication Date(Web):2017/12/01
DOI:10.1002/adfm.201703918
AbstractThis study reveals the mechanism of the dual-emission properties for asymmetrical diphenylsulfone and diphenylketone derivatives. A series of asymmetrical diphenylketone and diphenylsulfone derivatives with dual-emission properties are designed and synthesized. By single crystal structure analyses, various photophysical studies, and 2D 1H–1H NOSEY NMR studies, the lower energy emission bands in the dual-emission spectra are successfully assigned to hydrogen-bonding-assisted intermolecular charge transfer emission. The emission properties of these compounds can easily be tuned in both solid state and solution state by destroying or strengthening the intermolecular hydrogen bonding. In addition, thermally activated delayed fluorescence characteristics for the intermolecular charge transfer emissions are also observed. The control of the intermolecular and intramolecular charge transfers serves as the basis for the generation of the white-light emission. For compound CPzPO, nearly pure white-light emission with CIE coordinates of (0.31, 0.32) is easily achieved by precipitation from dichloromethane and hexane mixed solvent system. These results clearly give an insight into the dual-emission properties and provide a rational strategy for the design and synthesis of single-component white-light-emitting materials and mechanoresponsive light-emitting materials.
Co-reporter:S. M. Ali Fateminia;Zhu Mao;Shidang Xu;Dr. Zhiyong Yang;Dr. Zhenguo Chi;Dr. Bin Liu
Angewandte Chemie 2017 Volume 129(Issue 40) pp:12328-12332
Publication Date(Web):2017/09/25
DOI:10.1002/ange.201705945
AbstractPersistent room-temperature phosphorescence (RTP) in pure organic materials has attracted great attention because of their unique optical properties. The design of organic materials with bright red persistent RTP remains challenging. Herein, we report a new design strategy for realizing high brightness and long lifetime of red-emissive RTP molecules, which is based on introducing an alkoxy spacer between the hybrid units in the molecule. The spacer offers easy Br−H bond formation during crystallization, which also facilitates intermolecular electron coupling to favor persistent RTP. As the majority of RTP compounds have to be confined in a rigid environment to quench nonradiative relaxation pathways for bright phosphorescence emission, nanocrystallization is used to not only rigidify the molecules but also offer the desirable size and water-dispersity for biomedical applications.
Co-reporter:S. M. Ali Fateminia;Zhu Mao;Shidang Xu;Dr. Zhiyong Yang;Dr. Zhenguo Chi;Dr. Bin Liu
Angewandte Chemie International Edition 2017 Volume 56(Issue 40) pp:12160-12164
Publication Date(Web):2017/09/25
DOI:10.1002/anie.201705945
AbstractPersistent room-temperature phosphorescence (RTP) in pure organic materials has attracted great attention because of their unique optical properties. The design of organic materials with bright red persistent RTP remains challenging. Herein, we report a new design strategy for realizing high brightness and long lifetime of red-emissive RTP molecules, which is based on introducing an alkoxy spacer between the hybrid units in the molecule. The spacer offers easy Br−H bond formation during crystallization, which also facilitates intermolecular electron coupling to favor persistent RTP. As the majority of RTP compounds have to be confined in a rigid environment to quench nonradiative relaxation pathways for bright phosphorescence emission, nanocrystallization is used to not only rigidify the molecules but also offer the desirable size and water-dispersity for biomedical applications.
Co-reporter:Qiuyi Huang;Tao Yu;Zongliang Xie;Wenlang Li;Leyu Wang;Siwei Liu;Yi Zhang;Jiarui Xu;Matthew P. Aldred
Journal of Materials Chemistry C 2017 vol. 5(Issue 45) pp:11867-11872
Publication Date(Web):2017/11/23
DOI:10.1039/C7TC03404K
In this study, loosely packed crystals with the building blocks of aggregation induced emission (AIE)-active TPE-MN molecules were constructed with the assistance of intermolecular hydrogen bonding. The AIE properties of the compound TPE-MN were studied. From single crystal analyses, a sandwich-like crystal structure with tightly packed areas (TPE moieties) and loosely packed areas was observed. Nevertheless, the TPE-MN crystals display non-emissive properties in the loosely packed crystalline state. Differential scanning calorimetry (DSC) studies, powder X-ray diffraction analyses and various photophysical studies further reveal that the loosely packed crystal structure can provide enough space for significant molecular rotations and vibrations to occur, which leads to emission quenching. By breaking the loosely packed crystal structure with mechanical force or UV irradiation, the emission band with a maximum at ca. 562 nm can be turned on. These results can serve as a basis for constructing multi-responsive materials with turn-on emissive properties.
Co-reporter:Qiuyi Huang;Tao Yu;Zongliang Xie;Wenlang Li;Leyu Wang;Siwei Liu;Yi Zhang;Jiarui Xu;Matthew P. Aldred
Journal of Materials Chemistry C 2017 vol. 5(Issue 45) pp:11867-11872
Publication Date(Web):2017/11/23
DOI:10.1039/C7TC03404K
In this study, loosely packed crystals with the building blocks of aggregation induced emission (AIE)-active TPE-MN molecules were constructed with the assistance of intermolecular hydrogen bonding. The AIE properties of the compound TPE-MN were studied. From single crystal analyses, a sandwich-like crystal structure with tightly packed areas (TPE moieties) and loosely packed areas was observed. Nevertheless, the TPE-MN crystals display non-emissive properties in the loosely packed crystalline state. Differential scanning calorimetry (DSC) studies, powder X-ray diffraction analyses and various photophysical studies further reveal that the loosely packed crystal structure can provide enough space for significant molecular rotations and vibrations to occur, which leads to emission quenching. By breaking the loosely packed crystal structure with mechanical force or UV irradiation, the emission band with a maximum at ca. 562 nm can be turned on. These results can serve as a basis for constructing multi-responsive materials with turn-on emissive properties.
Co-reporter:Bingjia Xu;Haozhong Wu;Junru Chen;Zhan Yang;Zhiyong Yang;Yuan-Chun Wu;Yi Zhang;Chongjun Jin;Po-Yen Lu;Siwei Liu;Jiarui Xu;Matthew Aldred
Chemical Science (2010-Present) 2017 vol. 8(Issue 3) pp:1909-1914
Publication Date(Web):2017/02/28
DOI:10.1039/C6SC03038F
Two heavy atom-free luminophores (SHB2t and SDB2t) with simple molecular structures have been synthesized via Suzuki coupling reactions in which both display white-light emission with prompt fluorescence and room temperature phosphorescence (RTP) in the solid state. The impressive RTP of the luminophores is produced by a synergistic effect of the strong intermolecular hydrogen bonding in addition to the spin–orbit coupling of the sulfonyl oxygen atoms and the moderate singlet-triplet energy gaps (ΔEST). These factors facilitate the intersystem crossing (ISC) process to generate triplet excitons in which the molecular conformations become immobilized to effectively suppress radiationless decay. Under the stimuli of mechanical force and solvent vapor, the RTP of SHB2t and SDB2t can be simply turned off and on by breaking and reforming the robust hydrogen bonding, which leads to remarkable and reversible mechanochromism between white and deep-blue emission. Moreover, two different thermochromic processes have been observed for the pristine and ground samples of SDB2t, in which a tricolor switching system between white, deep-blue and blue emission has been successfully achieved through the sequential control of grinding, heating and fuming. From detailed studies we have determined that the mechanism for the thermochromism of SDB2t is correlated with the rearrangement of the white-light emitting molecules to a new packing mode without RTP emission.
Co-reporter:Depei Ou, Tao Yu, Zhiyong Yang, Tiangang Luan, Zhu Mao, Yi Zhang, Siwei Liu, Jiarui Xu, Zhenguo Chi and Martin R. Bryce
Chemical Science 2016 vol. 7(Issue 8) pp:5302-5306
Publication Date(Web):26 Apr 2016
DOI:10.1039/C6SC01205A
A dichloro-substituted triphenylethylene derivative (TrPECl2) with aggregation-induced emission (AIE), photochromism and photoresponsive wettability has been synthesized. The new compound shows fast-response photochromic behaviour with good ON/OFF repeatability by utilizing a proposed stilbene-type intramolecular photocyclization in the solid state. Compared with the more usual diphenylethylene derivatives, the photochromic properties of the triphenylethylene derivative are much more striking and easier to achieve. The triphenylethylene derivative also displays AIE properties leading to strong fluorescence in the solid state. Therefore, both the ultraviolet-visible absorption and fluorescence emission are drastically changed during the photochromic processes. Furthermore, the morphology of the TrPECl2 microcrystalline surface could be controlled by irradiation. The wettability of the surface could be drastically decreased with contact angles of a water droplet changing from 73° to 118°. The triphenylethylene derivative with a simple molecular structure is, therefore, attractive for multifunctional materials.
Co-reporter:Bingjia Xu, Wenlang Li, Jiajun He, Sikai Wu, Qiangzhong Zhu, Zhiyong Yang, Yuan-Chun Wu, Yi Zhang, Chongjun Jin, Po-Yen Lu, Zhenguo Chi, Siwei Liu, Jiarui Xu and Martin R. Bryce
Chemical Science 2016 vol. 7(Issue 8) pp:5307-5312
Publication Date(Web):26 Apr 2016
DOI:10.1039/C6SC01325B
Although bright organic mechanoluminescence (ML) has been observed for a few luminophores with aggregation-induced emission (AIE), details of the positive effect of AIE on ML performance remain unclear and a feasible design principle for AIE-ML compounds has not yet been presented. Herein, an effective strategy for the molecular design of efficient AIE-ML materials is demonstrated, based on tetraphenylethene (TPE) building blocks with formyl substituents, which yield non-centrosymmetric crystal structures with prominent piezoelectric properties for molecular excitation combined with AIE features for intense emission. Following this approach, three AIE-active compounds have been developed and are found to show unique ML characteristics. Furthermore, the results of single crystal X-ray analysis and density functional theory (DFT) calculations suggest that the ML performance would probably be further enhanced by creating molecules with larger dipolar moments and enhanced AIE properties.
Co-reporter:Yige Qi, Juan Zhao, Xu Wang, Junsheng Yu, Zhenguo Chi
Organic Electronics 2016 Volume 36() pp:185-191
Publication Date(Web):September 2016
DOI:10.1016/j.orgel.2016.05.043
•A PHOLED with high efficiency and low efficiency roll-off was realized.•Emission process was studied by single-carrier devices and PL transient decay curves.•High EQE is due to the efficient utilization of triplets via RISC and FRET.•High J1/2 is ascribed to the bipolar TADF host and FRET.Phosphorescent organic light-emitting devices (PHOLEDs) with high efficiency and low efficiency roll-off were fabricated. The emissive layer was composed of a thermally activated delayed fluorescence (TADF) material 4,5-bis(carbazol-9-yl)-1,2-dicyanobenzene (2CzPN) as host and an orange iridium complex bis(4-tert-butyl-2-phenylbenzothiozolato-N,C2′)iridium(III)(acetylacetonate) [(tbt)2Ir(acac)] as dopant. At a low dopant concentration of 1 wt%, a PHOLED without light extraction optimization achieved a maximum power efficiency of 42.1 lm/W, a luminance efficiency of 77.9 cd/A and an external quantum efficiency (EQE) of 26.8%, respectively. Meanwhile, the EQE maintained 26.6% at 1000 cd/m2 and 25.8% at 5000 cd/m2, respectively. Moreover, a critical current density of 300 mA/cm2 was realized, indicating significantly improved efficiency roll-off. The efficient utilization of triplet excitons on 2CzPN for phosphorescence via reverse inter-system crossing of 2CzPN followed by Fӧrster resonance energy transfer from 2CzPN to (tbt)2Ir(acac) is responsible for the superior performance.
Co-reporter:Bingjia Xu, Jiajun He, Yingxiao Mu, Qiangzhong Zhu, Sikai Wu, Yifan Wang, Yi Zhang, Chongjun Jin, Changcheng Lo, Zhenguo Chi, Alan Lien, Siwei Liu and Jiarui Xu
Chemical Science 2015 vol. 6(Issue 5) pp:3236-3241
Publication Date(Web):18 Mar 2015
DOI:10.1039/C5SC00466G
Organic materials exhibiting mechanoluminescence (ML) are promising for usage in displays, lighting and sensing. However, the mechanism for ML generation remains unclear, and the light-emitting performance of organic ML materials in the solid state has been severely limited by an aggregation-caused quenching (ACQ) effect. Herein, we present two strongly photoluminescent polymorphs (i.e., Cg and Cb) with distinctly different ML activities based on a tetraphenylethene derivative P4TA. As an aggregation-induced emission (AIE) emitter, P4TA perfectly surmounted the ACQ, making the resultant block-like crystals in the Cg phase exhibit brilliant green ML under daylight at room temperature. The ML-inactive prism-like crystals Cb can also have their ML turned on by transitioning toward Cg with the aid of dichloromethane vapor. Moreover, the Cg polymorph shows ML and mechanochromism simultaneously and respectively without and with UV irradiation under a force stimulus, thus suggesting a feasible design direction for the development of efficient and multifunctional ML materials.
Co-reporter:Qingyun Lu, Xiaofang Li, Jun Li, Zhiyong Yang, Bingjia Xu, Zhenguo Chi, Jiarui Xu and Yi Zhang
Journal of Materials Chemistry A 2015 vol. 3(Issue 6) pp:1225-1234
Publication Date(Web):20 Nov 2014
DOI:10.1039/C4TC02165G
Three tetraphenylvinyl-capped ethane derivatives with 0, 1, and 2 cyano groups at the ethane moiety, namely, biTPE, biTPE-CN, and TPE-CN, respectively, were synthesized and characterized via photoluminescence, ultraviolet-visible absorption, wide-angle X-ray diffraction, fluorescence lifetime, and other techniques. The results indicate that the compounds possess piezofluorochromic properties and exhibit aggregation-induced emission enhancement. The distinct piezofluorochromic properties of all three compounds were reversible upon grinding and fuming. The introduction of cyano groups to the molecular structures of the derivatives significantly enhanced their piezofluorochromic activity. The relationship between structure and property was studied in detail. The results obtained will be of great help in understanding the piezofluorochromic mechanism and designing new piezofluorochromic materials.
Co-reporter:Shidang Xu;Dr. Tingting Liu;Dr. Yingxiao Mu;Dr. Yi-Fan Wang; Zhenguo Chi;Dr. Chang-Cheng Lo; Siwei Liu; Yi Zhang;Dr. Alan Lien; Jiarui Xu
Angewandte Chemie International Edition 2015 Volume 54( Issue 3) pp:874-878
Publication Date(Web):
DOI:10.1002/anie.201409767
Abstract
Compounds displaying delayed fluorescence (DF), from severe concentration quenching, have limited applications as nondoped organic light-emitting diodes and material sciences. As a nondoped fluorescent emitter, aggregation-induced emission (AIE) materials show high emission efficiency in their aggregated states. Reported herein is an AIE-active, DF compound in which the molecular interaction is modulated, thereby promoting triplet harvesting in the solid state with a high photoluminescence quantum yield of 93.3 %, which is the highest quantum yield, to the best of our knowledge, for long-lifetime emitters. Simultaneously, the compound with asymmetric molecular structure exhibited strong mechanoluminescence (ML) without pretreatment in the solid state, thus exploiting a design and synthetic strategy to integrate the features of DF, AIE, and ML into one compound.
Co-reporter:Shidang Xu;Dr. Tingting Liu;Dr. Yingxiao Mu;Dr. Yi-Fan Wang; Zhenguo Chi;Dr. Chang-Cheng Lo; Siwei Liu; Yi Zhang;Dr. Alan Lien; Jiarui Xu
Angewandte Chemie 2015 Volume 127( Issue 3) pp:888-892
Publication Date(Web):
DOI:10.1002/ange.201409767
Abstract
Compounds displaying delayed fluorescence (DF), from severe concentration quenching, have limited applications as nondoped organic light-emitting diodes and material sciences. As a nondoped fluorescent emitter, aggregation-induced emission (AIE) materials show high emission efficiency in their aggregated states. Reported herein is an AIE-active, DF compound in which the molecular interaction is modulated, thereby promoting triplet harvesting in the solid state with a high photoluminescence quantum yield of 93.3 %, which is the highest quantum yield, to the best of our knowledge, for long-lifetime emitters. Simultaneously, the compound with asymmetric molecular structure exhibited strong mechanoluminescence (ML) without pretreatment in the solid state, thus exploiting a design and synthetic strategy to integrate the features of DF, AIE, and ML into one compound.
Co-reporter:Bingjia Xu, Jiajun He, Yang Liu, Bin Xu, Qiangzhong Zhu, Mingyuan Xie, Zebo Zheng, Zhenguo Chi, Wenjing Tian, Chongjun Jin, Fuli Zhao, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2014 vol. 2(Issue 17) pp:3416-3428
Publication Date(Web):22 Jan 2014
DOI:10.1039/C3TC32052A
Two novel quadrupolar D–π–D type two-photon absorption (2PA) luminophores PA2F4H8E8 and AnA2F4H8E8 were synthesized by Wittig–Horner reaction in high yields. By using distyrylbenzene as the π-bridge center, PA2F4H8E8 shows two-photon absorption aggregation-induced emission enhancement (2PA-AIEE) and exhibits exceptionally large 2PA and 2PA action cross-sections up to ∼6300 GM and ∼1400 GM at 800 nm in THF, respectively. A non-doped electroluminescent (EL) device of PA2F4H8E8 displays good performance with an extremely low turn-on voltage of 2.6 V and a high brightness of 9837 cd m−2.
Co-reporter:Chunping Ma, Bingjia Xu, Gaoyi Xie, Jiajun He, Xie Zhou, Bangyin Peng, Long Jiang, Bin Xu, Wenjing Tian, Zhenguo Chi, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2014 vol. 50(Issue 55) pp:7374-7377
Publication Date(Web):16 May 2014
DOI:10.1039/C4CC01012D
A novel luminophore TPENSOH was facilely synthesized from the building blocks of tetraphenylethylene and 6-hydroxylbenzothiazole and exhibited unique AIE properties. This new dye was found to show a remarkable and reversible four-color switching based on a single molecule in the solid state.
Co-reporter:Chunping Ma;Qingqing Ling;Shidang Xu;Hongni Zhu;Ge Zhang;Xie Zhou;Siwei Liu;Yi Zhang;Jiarui Xu
Macromolecular Bioscience 2014 Volume 14( Issue 2) pp:235-243
Publication Date(Web):
DOI:10.1002/mabi.201300259
A series of new homopolymers with various degrees of polymerization derived from vinyl tetraphenylethene, that is, poly[2-(4-vinylphenyl)ethene-1,1,2-triyl)tribenzene] homopolymers, is synthesized by reversible addition–fragmentation chain transfer (RAFT) polymerization. The homopolymers exhibit a significant aggregation-induced emission (AIE) effect and an ability to assemble themselves into AIE polymer nanoparticles (NPs) during precipitation in a water/tetrahydrofuran (THF) mixture. The NPs also exhibit good dispersibility, stability, and biocompatibility. The AIE polymer NPs are used in imaging studies of HeLa cells.
Co-reporter:Miao Luo, Xie Zhou, Zhenguo Chi, Siwei Liu, Yi Zhang, Jiarui Xu
Dyes and Pigments 2014 Volume 101() pp:74-84
Publication Date(Web):February 2014
DOI:10.1016/j.dyepig.2013.08.026
•Two novel aggregation-induced emission compounds were synthesized.•The compounds possess different gelation behavior in organic solvents.•Their emission was reversibly changed with the gel–solution transition.•The emission color of one compound could be switched by external stimuli.•Both of them possessed mesomorphic properties.Two novel aggregation-induced emission compounds derived from tetraphenylethylene and gallic acid were synthesized and characterized. Both of the emission compounds possessed mesomorphic properties and exhibited mesomorphic phases over a wide temperature range and the thermal-induced mesomorphic transition from metastable to stable phases accompanied by a change of the luminescent color. The mesomorphic transition may be ascribed to liquid crystalline phase transition. The emission compounds possess different gelation behavior in organic solvents. The emission intensities of the emission compounds can be reversibly changed with the gel–solution transition by alternate cooling and heating. Moreover, the color and emission of these organogelators can be repeatedly switched by various external stimuli including pressing, heating and solvent-fuming. These new compounds may offer potential as external stimuli-responsive materials.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2013 vol. 1(Issue 21) pp:3376-3390
Publication Date(Web):13 Mar 2013
DOI:10.1039/C3TC30316K
Mechanochromic luminescent metal complexes have recently attracted considerable interest as smart materials for use in the fields of luminescence switches, mechanosensors, mechanohistory indicators, security papers, optoelectronic devices, and data storage. In this review, recent advancements in metal complex mechanochromic luminescence are summarized. The majority of the reported mechanochromic luminescent metal complex systems are discussed, including Zn(II), Au(I), Pt(II), Ag(I), Cu(I), Al(III), and Ir(III) complexes. Aggregation-induced emission (AIE) complexes are described based on the existence of a structural relationship between AIE compounds and mechanochromism. It is expected that AIE complexes may become important alternative sources of mechanochromic luminescent complexes.
Co-reporter:Bingjia Xu, Mingyuan Xie, Jiajun He, Bin Xu, Zhenguo Chi, Wenjing Tian, Long Jiang, Fuli Zhao, Siwei Liu, Yi Zhang, Zhizhan Xu and Jiarui Xu
Chemical Communications 2013 vol. 49(Issue 3) pp:273-275
Publication Date(Web):13 Nov 2012
DOI:10.1039/C2CC36806D
A novel aggregation- and crystallization-induced emission luminophore (ENPOMe) containing tetraphenylethene and acrylonitrile moieties with high fluorescence efficiency (ΦF of up to 0.85) has been easily synthesized. ENPOMe has an exceptionally large two-photon absorption cross section (σ) of 5548 GM, and exhibits striking multi-stimuli-responsive single- and two-photon fluorescence switching with excellent reversibility in the solid state.
Co-reporter:Zhenguo Chi, Xiqi Zhang, Bingjia Xu, Xie Zhou, Chunping Ma, Yi Zhang, Siwei Liu and Jiarui Xu
Chemical Society Reviews 2012 vol. 41(Issue 10) pp:3878-3896
Publication Date(Web):26 Mar 2012
DOI:10.1039/C2CS35016E
Mechanofluorochromic materials, which are dependent on changes in physical molecular packing modes, have attracted considerable interest over the past ten years. In this review, recent progress in the area of pure organic mechanofluorochromism is summarized, and majority of the reported organic mechanofluorochromic systems are discussed, along with their derived structure–property relationships. The existence of a structural relationship between aggregation-induced emission compounds and mechanofluorochromism is recognized based on our recent results, which considered aggregation-induced emission compounds as a well of mechanofluorochromic materials. The established structure–property relationship will guide researchers in identifying and synthesizing more mechanofluorochromic materials.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Bingjia Xu, Chengjian Chen, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2012 vol. 22(Issue 35) pp:18505-18513
Publication Date(Web):20 Jul 2012
DOI:10.1039/C2JM33140C
Distyrylanthracene derivatives, AnP3 and AnP3P with triphenylethylene end-groups, and AnP4 and AnP4P with tetraphenylethylene end-groups, were synthesized and characterized using nuclear magnetic resonance, mass spectrometry, elemental analysis, photoluminescence, ultraviolet-visible absorption, wide-angle X-ray diffraction, differential scanning calorimetry and other techniques. The results show that the piezofluorochromic properties of these four aggregation-induced enhanced emission (AIEE) compounds were influenced significantly by the structures of the end-groups in the molecules. The AnP4 and AnP4P derivatives with tetraphenylethylene end-groups exhibited distinct piezofluorochromic properties, which might be switched reversibly upon pressing or annealing because of crystalline-amorphous phase transformation. Thus, we propose that those AIEE compounds that contain steric hindrance groups may exhibit evident piezofluorochromic activities.
Co-reporter:Chengjian Chen, Jin-Yun Liao, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Dai-Bin Kuang, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2012 vol. 22(Issue 18) pp:8994-9005
Publication Date(Web):06 Mar 2012
DOI:10.1039/C2JM30254C
Four novel D–D–π–A configuration metal-free organic dyes (C3, P2, C2 and P3) with triphenylethylene phenothiazine moieties or triphenylethylene carbazole moieties as additional electron donors for dye-sensitized solar cells (DSSCs) have been synthesized. The cells based on C3, P2, C2 and P3 dyes with efficiencies of 2.14%, 2.69%, 5.51% and 6.55%, respectively, are obtained. The P3 based cell exhibits the highest efficiency of 6.55% accompanied by a short-circuit current density (Jsc) of 12.18 mA cm−2, a rather high open-circuit photovoltage (Voc) of 826 mV, and a fill factor (ff) of 0.65, performances which are remarkable in the DSSCs based on metal-free organic dyes. The twisted non-planar configuration in P3 decelerates the charge recombination in the charge-separated state and hence contributes to the improvement of the performance of DSSCs.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Bingjia Xu, Long Jiang, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Chemical Communications 2012 vol. 48(Issue 88) pp:10895-10897
Publication Date(Web):18 Sep 2012
DOI:10.1039/C2CC36263E
A series of remarkable multifunctional 9,10-distyrylanthracene derivatives (DSAn, n = 7–12) was synthesized. All derivatives possess typical aggregation-induced emission (AIE) property. Some of the derivatives exhibit multifunctional properties, including AIE, mechanofluorochromism, vapochromism, thermochromism, and mesomorphism, which are rarely found to exist simultaneously in a single compound.
Co-reporter:Chengjian Chen, Jin-Yun Liao, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Dai-Bin Kuang, Yi Zhang, Siwei Liu and Jiarui Xu
RSC Advances 2012 vol. 2(Issue 20) pp:7788-7797
Publication Date(Web):30 Jul 2012
DOI:10.1039/C2RA20819A
A novel series of highly similar and comparable metal-free organic dyes have been designed and synthesized for dye-sensitized solar cells (DSSCs). The end-capped groups, namely, diphenylethylene, triphenylethylene, and tetraphenylethylene, have significant effects on the performance of DSSCs. The DSSC based on a triphenylethylene end-capped dye exhibits the highest power conversion efficiency (η) of 6.29%, whereas that based on a tetraphenylethylene end-capped dye has the highest open-circuit photovoltage (Voc) of 804 mV. The Voc of the DSSCs can be greatly improved upon the incorporation of a twisted non-planar aggregation-induced emission (AIE) moiety in the molecular structure of the dyes. The triphenylethylene group with a moderately twisted non-planar structure is found to be suitable for the improvement of the power conversion efficiency. The dyes exhibit an aggregation-caused emission quenching effect, i.e., the dyes do not emit light after being adsorbed on TiO2 films, although they contain aggregation-induced emission triphenylethylene and tetraphenylethylene moieties.
Co-reporter:Xie Zhou, Haiyin Li, Zhenguo Chi, Xiqi Zhang, Jianyong Zhang, Bingjia Xu, Yi Zhang, Siwei Liu and Jiarui Xu
New Journal of Chemistry 2012 vol. 36(Issue 3) pp:685-693
Publication Date(Web):13 Dec 2011
DOI:10.1039/C1NJ20782B
A new piezofluorochromic aggregation-induced emission compound was synthesized. The compound had morphology-alterable emission property and its amorphous and crystalline aggregates with various emissions were obtained through evaporation from the solutions in different solvent systems. The spectroscopic properties and morphological structures of the compound were reversed upon pressing and annealing (or fuming). The results show that the piezofluorochromic nature is generated through crystalline–amorphous phase transformation under external pressure. The reason for the phase transformation is ascribed to the twisted conformation of the molecule which leads to poor solid molecular packing and formation of some cavities in the interfaces of lamellar layers, as confirmed by single crystal X-ray diffraction analysis.
Co-reporter:Xiaofang Li, Xiqi Zhang, Zhenguo Chi, Xiaojuan Chao, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Analytical Methods 2012 vol. 4(Issue 10) pp:3338-3343
Publication Date(Web):16 Aug 2012
DOI:10.1039/C2AY25564B
A novel probe incorporating tetraphenylethylene and benzoquinone into a molecule was synthesized and studied for the selective detection of biothiols. The probe was found to have a highly selective response to biothiols through a thiol–ene click-reaction with fluorescence turn-on feature. The observable color changes before and after biothiol addition indicated that the probe was suitable for naked-eye biothiol detection.
Co-reporter:Xie Zhou;Hai-yin Li;Zhen-guo Chi;Bing-jia Xu;Xi-qi Zhang
Journal of Fluorescence 2012 Volume 22( Issue 2) pp:565-572
Publication Date(Web):2012 March
DOI:10.1007/s10895-011-0990-4
A novel piezochromic fluorescent (PCF) compound with aggregation-induced emission (AIE) effect and morphology-alterable emission property was developed. The amorphous and crystalline aggregates were obtained, and their spectroscopic properties and morphological structures were reversibly and repeatedly exhibited upon pressing (fuming) or annealing. The piezochromic fluorescent nature was generated through crystalline-amorphous phase transformation. It was proposed that AIE compounds existing a twisted propeller-shaped conformation will exhibit PCF activity. The common relationship betweeen AIE and PCF established will guide researchers in identifying and synthesizing more piezochromic fluorescent materials.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Xie Zhou, Siwei Liu, Yi Zhang, and Jiarui Xu
The Journal of Physical Chemistry C 2012 Volume 116(Issue 44) pp:23629-23638
Publication Date(Web):October 19, 2012
DOI:10.1021/jp306452n
Distyrylanthracene derivatives (AnPCz and AnPCz3) with monocarbazolyl and tricarbazolyl groups were synthesized and characterized via nuclear magnetic resonance, mass spectrometry, elemental analysis, photoluminescence, ultraviolet absorption, wide-angle X-ray diffraction, and other techniques. Another compound, distyrylanthracene (AnP), without any carbazolyl group was synthesized for comparison. The results show that the piezofluorochromic properties of the three aggregation-enhanced emission (AEE) compounds were significantly influenced by the variety of carbazolyl groups in the molecular structures. Compounds AnPCz and AnPCz3 exhibited distinct piezofluorochromic properties and switched reversibly upon grinding–annealing or grinding–fuming. The piezofluorochromic activity can be greatly enhanced by the introduction of carbazole groups in the distyrylanthracene AEE structure. The general structure–property relationships established in this study will help researchers to identify and synthesize more piezofluorochromic materials.
Co-reporter:Haiyin Li, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2011 vol. 21(Issue 11) pp:3760-3767
Publication Date(Web):31 Jan 2011
DOI:10.1039/C0JM02571B
New compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties are synthesized by the Wittig–Horner reaction. The compounds exhibit weak emission in good solvents, but strong fluorescence in aggregates or in the solid state, indicating that they are aggregation-induced emission enhancement compounds. The symmetry of their molecular structure affects their aggregation structures and photoluminescence emission properties in aggregation. These compounds show high thermal stabilities with glass transition temperatures between 168–177 °C and decomposition temperatures between 521–537 °C. The HOMO levels of the compounds are in the region of 4.92–4.94 eV, very close to the work function of indium tin oxide anode (4.8–5.0 eV). One of the compounds exhibits obvious piezofluorochromic behavior. The piezofluorochromic nature is generated through changing the mode of molecular packing under external pressure.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Haiyin Li, Bingjia Xu, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2011 vol. 21(Issue 6) pp:1788-1796
Publication Date(Web):07 Dec 2010
DOI:10.1039/C0JM02824J
A novel class of compounds containing tetraphenylethylene and dicarbazolyl triphenylethylene moieties combined with different spacers is synthesized. The compounds exhibit high thermal stabilities and aggregation-induced emission properties. The different spacers lead to differences in spatial conformation structures and spatial electron distributions, and markedly affect the thermal and photophysical properties of the compounds. The size of the aggregates formed in water–THF mixtures decreases with increasing water fractions. The time-resolved emission decay behaviors of the synthesized compounds in water–THF mixtures with water fractions from 60% to 99% show three relaxation pathways in their fluorescence decays.
Co-reporter:Haiyin Li, Zhenguo Chi, Xiqi Zhang, Bingjia Xu, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2011 vol. 47(Issue 40) pp:11273-11275
Publication Date(Web):19 Sep 2011
DOI:10.1039/C1CC14642D
New thermally stable aggregation-induced emission enhancement compounds were synthesized. A non-doped red device showed a maximum brightness of 13535 cd m−2, a maximum current efficiency of 6.81 cd A−1, a maximum power efficiency of 4.96 lm W−1 and a low turn-on voltage of 4.3 V.
Co-reporter:Bingjia Xu, Zhenguo Chi, Xiqi Zhang, Haiyin Li, Chengjian Chen, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2011 vol. 47(Issue 39) pp:11080-11082
Publication Date(Web):30 Aug 2011
DOI:10.1039/C1CC13790E
A new ligand containing tetraphenylethylene and terpyridine moieties, and its zinc ion complex were synthesized. Both of them exhibit an aggregation-induced emission effect. Their colors and emissions can be smartly switched by various external stimuli including grinding, heating and solvent-fuming, as well as exposure to acid and base vapors.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Bingjia Xu, Haiyin Li, Zhiyong Yang, Xiaofang Li, Siwei Liu, Yi Zhang, Jiarui Xu
Dyes and Pigments 2011 Volume 89(Issue 1) pp:56-62
Publication Date(Web):April 2011
DOI:10.1016/j.dyepig.2010.09.003
A series of new aggregation-induced emission enhancement derivatives from bis(triphenylethylene) with strong blue-light-emitting properties and high thermal stability have been synthesized. Their maximum fluorescence emission wavelengths range between 464–468 nm, with fluorescence quantum yields of 0.58–0.88. Their glass transition temperatures range from 125 °C to 178 °C. The obtained experimental results demonstrate the different aggregation-induced emission enhancement phenomena caused by the effect of solvent and formation of both H- and J- aggregation states. An emitting device was fabricated using a bis(triphenylene) derivative in the emitting layer which exhibited a luminance efficiency of up to 2 cd/A with a maximum brightness of 548 cd/m2.
Co-reporter:Xi-qi Zhang;Zhen-guo Chi;Bing-jia Xu;Hai-yin Li;Wei Zhou
Journal of Fluorescence 2011 Volume 21( Issue 1) pp:133-140
Publication Date(Web):2011 January
DOI:10.1007/s10895-010-0697-y
Two cinnamic acid derivatives (CPA and CPC) containing carbazolyl triphenylethylene moiety have been synthesized and characterized. The two derivatives possessed aggregation-induced emission property. They exhibited different and interesting responsive behaviors to solvents, water and metal ions. Considering the structural differences between the two derivatives resulting in different interactions between their molecules and the various media was proposed as a possible explanation for these observations. The intermolecular interactions of CPC were much stronger than those of CPA, which promoted molecular association through intermolecular hydrogen bonding to form multimers. It was found that CPC and CPA exhibited high sensitivity to K+ and Mn2+, respectively. It is suggested that the derivatives have potential technological applications in chemosensor fields.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Jianyong Zhang, Haiyin Li, Bingjia Xu, Xiaofang Li, Siwei Liu, Yi Zhang, and Jiarui Xu
The Journal of Physical Chemistry B 2011 Volume 115(Issue 23) pp:7606-7611
Publication Date(Web):May 18, 2011
DOI:10.1021/jp202112e
A fluorescent compound, 9,10-bis(2-(10-hexyl-10H-phenothiazin-3-yl)vinyl) anthracene, has been synthesized and studied. The results show that the compound possesses piezofluorochromic properties as well as aggregation-induced emission enhancement effect. The spectroscopic properties and morphological structures are reversibly exhibited upon pressing (or grinding) or annealing (or fuming). The piezofluorochromic nature is generated through phase transformation under the stimulus of external pressure. The reason for the phase transformation caused by external pressure is ascribed to the twisted conformation of the molecule which leads to poor solid molecular packing and weak interactions in the interfaces of lamellar layers confirmed by its single-crystal X-ray diffraction analysis.
Co-reporter:Bingjia Xu, Zhenguo Chi, Haiyin Li, Xiqi Zhang, Xiaofang Li, Siwei Liu, Yi Zhang, and Jiarui Xu
The Journal of Physical Chemistry C 2011 Volume 115(Issue 35) pp:17574-17581
Publication Date(Web):July 28, 2011
DOI:10.1021/jp205525s
Aggregation-induced emission compounds containing triphenylethene and tetraphenylethene moieties with high thermal stability and good device properties have been synthesized. Their maximum fluorescence emission wavelengths are 469–493 nm in solid states. The glass transition temperatures range from 138 to 180 °C and the decomposition temperatures are 495–557 °C. The unoptimized device fabricated with the triphenylethene compound combined with three tetraphenylethene groups as emitters turns on at ∼6 V and the maximum luminance is observed at ∼1908 cd/m2 and 15.5 V. The electroluminescence peak of the device is at 474 nm and the Commission Internationale de l’Eclairage (CIE) chromaticity coordinate values are (0.18, 0.31) at 10 V.
Co-reporter:Dr. Xiqi Zhang; Zhenguo Chi;Dr. Haiyin Li;Dr. Bingjia Xu;Dr. Xiaofang Li;Wei Zhou;Dr. Siwei Liu; Yi Zhang ; Jiarui Xu
Chemistry – An Asian Journal 2011 Volume 6( Issue 3) pp:808-811
Publication Date(Web):
DOI:10.1002/asia.201000802
Co-reporter:Dr. Bingjia Xu; Zhenguo Chi; Jianyong Zhang;Dr. Xiqi Zhang;Dr. Haiyin Li;Dr. Xiaofang Li;Dr. Siwei Liu; Yi Zhang ; Jiarui Xu
Chemistry – An Asian Journal 2011 Volume 6( Issue 6) pp:1470-1478
Publication Date(Web):
DOI:10.1002/asia.201100211
Abstract
New fluorescent compounds containing triphenylethylene and tetraphenylethylene moieties were synthesized, and their piezofluorochromic and aggregation-induced emission behaviors were investigated. The results show that all compounds exhibit aggregation-induced emission characteristics and only the crystalline compound possesses piezofluorochromic properties. The color, emission spectra, and morphological structures of the one piezofluorochromic compound exhibit reversibility upon grinding and annealing (or fuming) treatments. The piezofluorochromic behaviors are caused by a change between different modes of solid state molecular packing under external pressure. The single crystal X-ray diffraction analysis reveals that the twisted conformation of the aggregation-induced emission compound leads to the formation of metastable crystal lattice with cavity which is readily destroyed under external pressure. A possible mechanism of piezofluorochromic phenomenon has been proposed.
Co-reporter:Xiqi Zhang, Zhiyong Yang, Zhenguo Chi, Meina Chen, Bingjia Xu, Chengcheng Wang, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 vol. 20(Issue 2) pp:292-298
Publication Date(Web):09 Nov 2009
DOI:10.1039/B910718E
A new cyanoacrylic acid derivative of carbazole-triphenylethylene as a fluorescent probe has been synthesized and characterized. The derivative exhibits not only aggregation-induced effect (AIE) properties, but also interesting fluorescence multi-responses to solvents, water, ethanol and metal ions due to its chemical structure. Responses of the compound solution in DMF to water can be explained in terms of H-bond, multimer and AIE effects. In addition, the derivative was found to be highly sensitive to potassium ions. It is suggested that the compound has potential applications in chemosensors.
Co-reporter:Bingjia Xu, Zhenguo Chi, Zhiyong Yang, Jingbo Chen, Shaozhi Deng, Haiyin Li, Xiaofang Li, Yi Zhang, Ningsheng Xu and Jiarui Xu
Journal of Materials Chemistry A 2010 vol. 20(Issue 20) pp:4135-4141
Publication Date(Web):15 Apr 2010
DOI:10.1039/C0JM00229A
A series of new aggregation-induced emission compounds with strong blue light-emitting properties derived from triphenylethylene were facilely synthesized by a Wittig–Horner reaction of bis(4-bromophenyl)methanone with diethyl 4-bromobenzylphosphonate, followed by a Suzuki reaction with arylboronic acids. Their maximum fluorescence emission wavelengths were 452–462 nm. The glass transition temperatures ranged from 70–145 °C, and the decomposition temperatures were 360–508 °C. The unoptimized device fabricated with benzofuranyl substituted compound as emitter turned on at ∼6 V, and the maximum luminance was ∼1500 cd m−2.
Co-reporter:Zhiyong Yang, Zhenguo Chi, Bingjia Xu, Haiyin Li, Xiqi Zhang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 vol. 20(Issue 35) pp:7352-7359
Publication Date(Web):03 Aug 2010
DOI:10.1039/C0JM00712A
A new class of carbazole derivatives was facilely synthesized by Wittig–Horner and Suzuki reactions, and their thermal and photophysical properties were investigated. They exhibited aggregation-induced emission enhancement (AIEE) characteristics and high thermal stability. The glass transition temperatures (Tg) of these compounds ranged from 178 to 231 °C, while their decomposition temperatures (Td) ranged from 496 to 535 °C. The solubility of the derivatives did not monotonically change with an increasing number of phenylene bridges, but exhibited a clear odd-even effect.
Co-reporter:Haiyin Li, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Zhiyong Yang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 vol. 20(Issue 29) pp:6103-6110
Publication Date(Web):16 Jun 2010
DOI:10.1039/C0JM00599A
A new class of compounds containing triarylamine and dicarbazolyl triphenylethylene moieties with high thermal stability and aggregation-induced emission enhancement properties was synthesized. The glass transition temperature and 5% weight loss temperature of 3B-TPA are up to 214.3 °C and 516.8 °C, respectively. The compounds exhibited significant photoinduced intramolecular charge-transfer properties. The aggregation considerably affected the π–π* transition and resulted in 6–7 nm red shift of the π–π* absorption wavelength at the peak in UV-vis spectra. The compounds could emit intense blue-green light in aggregated states.
Co-reporter:Zhiyong Yang, Zhenguo Chi, Tao Yu, Xiqi Zhang, Meina Chen, Bingjia Xu, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2009 vol. 19(Issue 31) pp:5541-5546
Publication Date(Web):19 Jun 2009
DOI:10.1039/B902802A
A new class of aggregation-induced emission (AIE) compounds with strong blue-light-emitting properties and a high thermal stability, derived from triphenylethylene carbazole, has been synthesized. Their glass transition temperatures range from 126–151 °C and the maximum fluorescence emission wavelengths are 451–466 nm.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Zhiyong Yang, Meina Chen, Bingjia Xu, Lin Zhou, Chengcheng Wang, Yi Zhang, Siwei Liu, Jiarui Xu
Optical Materials 2009 Volume 32(Issue 1) pp:94-98
Publication Date(Web):November 2009
DOI:10.1016/j.optmat.2009.06.009
A series of fluorescent compounds derived from carbazole were synthesized via the Wittig–Horner reaction. The compounds had high glass transition temperatures (Tg), in the region of 172–232 °C, and high decomposition temperatures (Td), ranging from 456 to 491 °C. The derivatives showed very high fluorescence efficiency in solution, with fluorescence quantum yields in the range of 0.88–1.00. The substituent effects on fluorescence emission differed between solution and solid state. In dichloromethane solutions, the substituents had only a minimal effect on the maximum emission wavelength of the compounds with the same bridge.
Co-reporter:Zhiyong Yang, Zhenguo Chi, Lin Zhou, Xiqi Zhang, Meina Chen, Bingjia Xu, Chengcheng Wang, Yi Zhang, Jiarui Xu
Optical Materials 2009 Volume 32(Issue 2) pp:398-401
Publication Date(Web):December 2009
DOI:10.1016/j.optmat.2009.06.011
A new series of fluorescent compounds containing tricarbazolyl groups have been synthesized. The compounds have very high glass transition temperatures in the range 243–266 °C, high decomposition temperatures of 506–527 °C, and exhibit strong blue fluorescence with maximum emission wavelengths at 445–457 nm. The compounds have good solubility in common solvents even though they contain rather rigid wholly aromatic structures. The thermal stability of these compounds exhibits a marked odd–even effect corresponding to the number of phenylene bridges in the compound. In the solid, the maximum photoluminescence emission wavelength with n odd have a slight bathochromic shift in comparison to those with n even.
Co-reporter:Zhenguo Chi;Xiqi Zhang;Yi Zhang ;Jiarui Xu
Journal of Applied Polymer Science 2008 Volume 110( Issue 5) pp:3001-3008
Publication Date(Web):
DOI:10.1002/app.28793
Abstract
A series of poly(ester imide)s mainly derived from N,N′-hexane-1,6-diylbistrimellitimides, 4,4′-dihydroxybenzophenone, and p-hydroxybenzoic acid were synthesized by a direct polycondensation method in benzenesulfonyl chloride, N,N′-dimethylformamide, and pyridine with different monomer feeding sequences. The molecular structures and properties of the resultant poly(ester imide)s were characterized with NMR, IR spectrometry, polarized light microscopy, wide-angle X-ray diffraction, differential scanning calorimetry, and thermogravimetric analysis. The results showed that the monomer feeding sequences had a great effect on the sequential structure of the molecular chains of the copolymers and consequently on their liquid-crystalline (LC) properties, fiber-forming capability, and other properties. Thus, it is probable that one could obtain an LC poly(ester imide) with given properties by controlling the monomer feeding sequence during the polycondensation process. © 2008 Wiley Periodicals, Inc. J Appl Polym Sci, 2008
Co-reporter:Qingyun Lu, Xiaofang Li, Jun Li, Zhiyong Yang, Bingjia Xu, Zhenguo Chi, Jiarui Xu and Yi Zhang
Journal of Materials Chemistry A 2015 - vol. 3(Issue 6) pp:NaN1234-1234
Publication Date(Web):2014/11/20
DOI:10.1039/C4TC02165G
Three tetraphenylvinyl-capped ethane derivatives with 0, 1, and 2 cyano groups at the ethane moiety, namely, biTPE, biTPE-CN, and TPE-CN, respectively, were synthesized and characterized via photoluminescence, ultraviolet-visible absorption, wide-angle X-ray diffraction, fluorescence lifetime, and other techniques. The results indicate that the compounds possess piezofluorochromic properties and exhibit aggregation-induced emission enhancement. The distinct piezofluorochromic properties of all three compounds were reversible upon grinding and fuming. The introduction of cyano groups to the molecular structures of the derivatives significantly enhanced their piezofluorochromic activity. The relationship between structure and property was studied in detail. The results obtained will be of great help in understanding the piezofluorochromic mechanism and designing new piezofluorochromic materials.
Co-reporter:Zhiyong Yang, Zhenguo Chi, Bingjia Xu, Haiyin Li, Xiqi Zhang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 - vol. 20(Issue 35) pp:NaN7359-7359
Publication Date(Web):2010/08/03
DOI:10.1039/C0JM00712A
A new class of carbazole derivatives was facilely synthesized by Wittig–Horner and Suzuki reactions, and their thermal and photophysical properties were investigated. They exhibited aggregation-induced emission enhancement (AIEE) characteristics and high thermal stability. The glass transition temperatures (Tg) of these compounds ranged from 178 to 231 °C, while their decomposition temperatures (Td) ranged from 496 to 535 °C. The solubility of the derivatives did not monotonically change with an increasing number of phenylene bridges, but exhibited a clear odd-even effect.
Co-reporter:Bingjia Xu, Zhenguo Chi, Zhiyong Yang, Jingbo Chen, Shaozhi Deng, Haiyin Li, Xiaofang Li, Yi Zhang, Ningsheng Xu and Jiarui Xu
Journal of Materials Chemistry A 2010 - vol. 20(Issue 20) pp:NaN4141-4141
Publication Date(Web):2010/04/15
DOI:10.1039/C0JM00229A
A series of new aggregation-induced emission compounds with strong blue light-emitting properties derived from triphenylethylene were facilely synthesized by a Wittig–Horner reaction of bis(4-bromophenyl)methanone with diethyl 4-bromobenzylphosphonate, followed by a Suzuki reaction with arylboronic acids. Their maximum fluorescence emission wavelengths were 452–462 nm. The glass transition temperatures ranged from 70–145 °C, and the decomposition temperatures were 360–508 °C. The unoptimized device fabricated with benzofuranyl substituted compound as emitter turned on at ∼6 V, and the maximum luminance was ∼1500 cd m−2.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Haiyin Li, Bingjia Xu, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2011 - vol. 21(Issue 6) pp:NaN1796-1796
Publication Date(Web):2010/12/07
DOI:10.1039/C0JM02824J
A novel class of compounds containing tetraphenylethylene and dicarbazolyl triphenylethylene moieties combined with different spacers is synthesized. The compounds exhibit high thermal stabilities and aggregation-induced emission properties. The different spacers lead to differences in spatial conformation structures and spatial electron distributions, and markedly affect the thermal and photophysical properties of the compounds. The size of the aggregates formed in water–THF mixtures decreases with increasing water fractions. The time-resolved emission decay behaviors of the synthesized compounds in water–THF mixtures with water fractions from 60% to 99% show three relaxation pathways in their fluorescence decays.
Co-reporter:Haiyin Li, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2011 - vol. 21(Issue 11) pp:NaN3767-3767
Publication Date(Web):2011/01/31
DOI:10.1039/C0JM02571B
New compounds containing triphenylamine-anthrylenevinylene and tetraphenylethene moieties are synthesized by the Wittig–Horner reaction. The compounds exhibit weak emission in good solvents, but strong fluorescence in aggregates or in the solid state, indicating that they are aggregation-induced emission enhancement compounds. The symmetry of their molecular structure affects their aggregation structures and photoluminescence emission properties in aggregation. These compounds show high thermal stabilities with glass transition temperatures between 168–177 °C and decomposition temperatures between 521–537 °C. The HOMO levels of the compounds are in the region of 4.92–4.94 eV, very close to the work function of indium tin oxide anode (4.8–5.0 eV). One of the compounds exhibits obvious piezofluorochromic behavior. The piezofluorochromic nature is generated through changing the mode of molecular packing under external pressure.
Co-reporter:Haiyin Li, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Zhiyong Yang, Xiaofang Li, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 - vol. 20(Issue 29) pp:NaN6110-6110
Publication Date(Web):2010/06/16
DOI:10.1039/C0JM00599A
A new class of compounds containing triarylamine and dicarbazolyl triphenylethylene moieties with high thermal stability and aggregation-induced emission enhancement properties was synthesized. The glass transition temperature and 5% weight loss temperature of 3B-TPA are up to 214.3 °C and 516.8 °C, respectively. The compounds exhibited significant photoinduced intramolecular charge-transfer properties. The aggregation considerably affected the π–π* transition and resulted in 6–7 nm red shift of the π–π* absorption wavelength at the peak in UV-vis spectra. The compounds could emit intense blue-green light in aggregated states.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Bingjia Xu, Long Jiang, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Chemical Communications 2012 - vol. 48(Issue 88) pp:NaN10897-10897
Publication Date(Web):2012/09/18
DOI:10.1039/C2CC36263E
A series of remarkable multifunctional 9,10-distyrylanthracene derivatives (DSAn, n = 7–12) was synthesized. All derivatives possess typical aggregation-induced emission (AIE) property. Some of the derivatives exhibit multifunctional properties, including AIE, mechanofluorochromism, vapochromism, thermochromism, and mesomorphism, which are rarely found to exist simultaneously in a single compound.
Co-reporter:Haiyin Li, Zhenguo Chi, Xiqi Zhang, Bingjia Xu, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2011 - vol. 47(Issue 40) pp:NaN11275-11275
Publication Date(Web):2011/09/19
DOI:10.1039/C1CC14642D
New thermally stable aggregation-induced emission enhancement compounds were synthesized. A non-doped red device showed a maximum brightness of 13535 cd m−2, a maximum current efficiency of 6.81 cd A−1, a maximum power efficiency of 4.96 lm W−1 and a low turn-on voltage of 4.3 V.
Co-reporter:Bingjia Xu, Wenlang Li, Jiajun He, Sikai Wu, Qiangzhong Zhu, Zhiyong Yang, Yuan-Chun Wu, Yi Zhang, Chongjun Jin, Po-Yen Lu, Zhenguo Chi, Siwei Liu, Jiarui Xu and Martin R. Bryce
Chemical Science (2010-Present) 2016 - vol. 7(Issue 8) pp:NaN5312-5312
Publication Date(Web):2016/04/26
DOI:10.1039/C6SC01325B
Although bright organic mechanoluminescence (ML) has been observed for a few luminophores with aggregation-induced emission (AIE), details of the positive effect of AIE on ML performance remain unclear and a feasible design principle for AIE-ML compounds has not yet been presented. Herein, an effective strategy for the molecular design of efficient AIE-ML materials is demonstrated, based on tetraphenylethene (TPE) building blocks with formyl substituents, which yield non-centrosymmetric crystal structures with prominent piezoelectric properties for molecular excitation combined with AIE features for intense emission. Following this approach, three AIE-active compounds have been developed and are found to show unique ML characteristics. Furthermore, the results of single crystal X-ray analysis and density functional theory (DFT) calculations suggest that the ML performance would probably be further enhanced by creating molecules with larger dipolar moments and enhanced AIE properties.
Co-reporter:Zhenguo Chi, Xiqi Zhang, Bingjia Xu, Xie Zhou, Chunping Ma, Yi Zhang, Siwei Liu and Jiarui Xu
Chemical Society Reviews 2012 - vol. 41(Issue 10) pp:NaN3896-3896
Publication Date(Web):2012/03/26
DOI:10.1039/C2CS35016E
Mechanofluorochromic materials, which are dependent on changes in physical molecular packing modes, have attracted considerable interest over the past ten years. In this review, recent progress in the area of pure organic mechanofluorochromism is summarized, and majority of the reported organic mechanofluorochromic systems are discussed, along with their derived structure–property relationships. The existence of a structural relationship between aggregation-induced emission compounds and mechanofluorochromism is recognized based on our recent results, which considered aggregation-induced emission compounds as a well of mechanofluorochromic materials. The established structure–property relationship will guide researchers in identifying and synthesizing more mechanofluorochromic materials.
Co-reporter:Bingjia Xu, Mingyuan Xie, Jiajun He, Bin Xu, Zhenguo Chi, Wenjing Tian, Long Jiang, Fuli Zhao, Siwei Liu, Yi Zhang, Zhizhan Xu and Jiarui Xu
Chemical Communications 2013 - vol. 49(Issue 3) pp:NaN275-275
Publication Date(Web):2012/11/13
DOI:10.1039/C2CC36806D
A novel aggregation- and crystallization-induced emission luminophore (ENPOMe) containing tetraphenylethene and acrylonitrile moieties with high fluorescence efficiency (ΦF of up to 0.85) has been easily synthesized. ENPOMe has an exceptionally large two-photon absorption cross section (σ) of 5548 GM, and exhibits striking multi-stimuli-responsive single- and two-photon fluorescence switching with excellent reversibility in the solid state.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2013 - vol. 1(Issue 21) pp:NaN3390-3390
Publication Date(Web):2013/03/13
DOI:10.1039/C3TC30316K
Mechanochromic luminescent metal complexes have recently attracted considerable interest as smart materials for use in the fields of luminescence switches, mechanosensors, mechanohistory indicators, security papers, optoelectronic devices, and data storage. In this review, recent advancements in metal complex mechanochromic luminescence are summarized. The majority of the reported mechanochromic luminescent metal complex systems are discussed, including Zn(II), Au(I), Pt(II), Ag(I), Cu(I), Al(III), and Ir(III) complexes. Aggregation-induced emission (AIE) complexes are described based on the existence of a structural relationship between AIE compounds and mechanochromism. It is expected that AIE complexes may become important alternative sources of mechanochromic luminescent complexes.
Co-reporter:Bingjia Xu, Jiajun He, Yingxiao Mu, Qiangzhong Zhu, Sikai Wu, Yifan Wang, Yi Zhang, Chongjun Jin, Changcheng Lo, Zhenguo Chi, Alan Lien, Siwei Liu and Jiarui Xu
Chemical Science (2010-Present) 2015 - vol. 6(Issue 5) pp:NaN3241-3241
Publication Date(Web):2015/03/18
DOI:10.1039/C5SC00466G
Organic materials exhibiting mechanoluminescence (ML) are promising for usage in displays, lighting and sensing. However, the mechanism for ML generation remains unclear, and the light-emitting performance of organic ML materials in the solid state has been severely limited by an aggregation-caused quenching (ACQ) effect. Herein, we present two strongly photoluminescent polymorphs (i.e., Cg and Cb) with distinctly different ML activities based on a tetraphenylethene derivative P4TA. As an aggregation-induced emission (AIE) emitter, P4TA perfectly surmounted the ACQ, making the resultant block-like crystals in the Cg phase exhibit brilliant green ML under daylight at room temperature. The ML-inactive prism-like crystals Cb can also have their ML turned on by transitioning toward Cg with the aid of dichloromethane vapor. Moreover, the Cg polymorph shows ML and mechanochromism simultaneously and respectively without and with UV irradiation under a force stimulus, thus suggesting a feasible design direction for the development of efficient and multifunctional ML materials.
Co-reporter:Zhiyong Yang, Zhenguo Chi, Tao Yu, Xiqi Zhang, Meina Chen, Bingjia Xu, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2009 - vol. 19(Issue 31) pp:NaN5546-5546
Publication Date(Web):2009/06/19
DOI:10.1039/B902802A
A new class of aggregation-induced emission (AIE) compounds with strong blue-light-emitting properties and a high thermal stability, derived from triphenylethylene carbazole, has been synthesized. Their glass transition temperatures range from 126–151 °C and the maximum fluorescence emission wavelengths are 451–466 nm.
Co-reporter:Bingjia Xu, Jiajun He, Yang Liu, Bin Xu, Qiangzhong Zhu, Mingyuan Xie, Zebo Zheng, Zhenguo Chi, Wenjing Tian, Chongjun Jin, Fuli Zhao, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2014 - vol. 2(Issue 17) pp:NaN3428-3428
Publication Date(Web):2014/01/22
DOI:10.1039/C3TC32052A
Two novel quadrupolar D–π–D type two-photon absorption (2PA) luminophores PA2F4H8E8 and AnA2F4H8E8 were synthesized by Wittig–Horner reaction in high yields. By using distyrylbenzene as the π-bridge center, PA2F4H8E8 shows two-photon absorption aggregation-induced emission enhancement (2PA-AIEE) and exhibits exceptionally large 2PA and 2PA action cross-sections up to ∼6300 GM and ∼1400 GM at 800 nm in THF, respectively. A non-doped electroluminescent (EL) device of PA2F4H8E8 displays good performance with an extremely low turn-on voltage of 2.6 V and a high brightness of 9837 cd m−2.
Co-reporter:Xiqi Zhang, Zhiyong Yang, Zhenguo Chi, Meina Chen, Bingjia Xu, Chengcheng Wang, Siwei Liu, Yi Zhang and Jiarui Xu
Journal of Materials Chemistry A 2010 - vol. 20(Issue 2) pp:NaN298-298
Publication Date(Web):2009/11/09
DOI:10.1039/B910718E
A new cyanoacrylic acid derivative of carbazole-triphenylethylene as a fluorescent probe has been synthesized and characterized. The derivative exhibits not only aggregation-induced effect (AIE) properties, but also interesting fluorescence multi-responses to solvents, water, ethanol and metal ions due to its chemical structure. Responses of the compound solution in DMF to water can be explained in terms of H-bond, multimer and AIE effects. In addition, the derivative was found to be highly sensitive to potassium ions. It is suggested that the compound has potential applications in chemosensors.
Co-reporter:Chunping Ma, Bingjia Xu, Gaoyi Xie, Jiajun He, Xie Zhou, Bangyin Peng, Long Jiang, Bin Xu, Wenjing Tian, Zhenguo Chi, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2014 - vol. 50(Issue 55) pp:NaN7377-7377
Publication Date(Web):2014/05/16
DOI:10.1039/C4CC01012D
A novel luminophore TPENSOH was facilely synthesized from the building blocks of tetraphenylethylene and 6-hydroxylbenzothiazole and exhibited unique AIE properties. This new dye was found to show a remarkable and reversible four-color switching based on a single molecule in the solid state.
Co-reporter:Bingjia Xu, Zhenguo Chi, Xiqi Zhang, Haiyin Li, Chengjian Chen, Siwei Liu, Yi Zhang and Jiarui Xu
Chemical Communications 2011 - vol. 47(Issue 39) pp:NaN11082-11082
Publication Date(Web):2011/08/30
DOI:10.1039/C1CC13790E
A new ligand containing tetraphenylethylene and terpyridine moieties, and its zinc ion complex were synthesized. Both of them exhibit an aggregation-induced emission effect. Their colors and emissions can be smartly switched by various external stimuli including grinding, heating and solvent-fuming, as well as exposure to acid and base vapors.
Co-reporter:Depei Ou, Tao Yu, Zhiyong Yang, Tiangang Luan, Zhu Mao, Yi Zhang, Siwei Liu, Jiarui Xu, Zhenguo Chi and Martin R. Bryce
Chemical Science (2010-Present) 2016 - vol. 7(Issue 8) pp:NaN5306-5306
Publication Date(Web):2016/04/26
DOI:10.1039/C6SC01205A
A dichloro-substituted triphenylethylene derivative (TrPECl2) with aggregation-induced emission (AIE), photochromism and photoresponsive wettability has been synthesized. The new compound shows fast-response photochromic behaviour with good ON/OFF repeatability by utilizing a proposed stilbene-type intramolecular photocyclization in the solid state. Compared with the more usual diphenylethylene derivatives, the photochromic properties of the triphenylethylene derivative are much more striking and easier to achieve. The triphenylethylene derivative also displays AIE properties leading to strong fluorescence in the solid state. Therefore, both the ultraviolet-visible absorption and fluorescence emission are drastically changed during the photochromic processes. Furthermore, the morphology of the TrPECl2 microcrystalline surface could be controlled by irradiation. The wettability of the surface could be drastically decreased with contact angles of a water droplet changing from 73° to 118°. The triphenylethylene derivative with a simple molecular structure is, therefore, attractive for multifunctional materials.
Co-reporter:Chengjian Chen, Jin-Yun Liao, Zhenguo Chi, Bingjia Xu, Xiqi Zhang, Dai-Bin Kuang, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2012 - vol. 22(Issue 18) pp:NaN9005-9005
Publication Date(Web):2012/03/06
DOI:10.1039/C2JM30254C
Four novel D–D–π–A configuration metal-free organic dyes (C3, P2, C2 and P3) with triphenylethylene phenothiazine moieties or triphenylethylene carbazole moieties as additional electron donors for dye-sensitized solar cells (DSSCs) have been synthesized. The cells based on C3, P2, C2 and P3 dyes with efficiencies of 2.14%, 2.69%, 5.51% and 6.55%, respectively, are obtained. The P3 based cell exhibits the highest efficiency of 6.55% accompanied by a short-circuit current density (Jsc) of 12.18 mA cm−2, a rather high open-circuit photovoltage (Voc) of 826 mV, and a fill factor (ff) of 0.65, performances which are remarkable in the DSSCs based on metal-free organic dyes. The twisted non-planar configuration in P3 decelerates the charge recombination in the charge-separated state and hence contributes to the improvement of the performance of DSSCs.
Co-reporter:Bingjia Xu, Haozhong Wu, Junru Chen, Zhan Yang, Zhiyong Yang, Yuan-Chun Wu, Yi Zhang, Chongjun Jin, Po-Yen Lu, Zhenguo Chi, Siwei Liu, Jiarui Xu and Matthew Aldred
Chemical Science (2010-Present) 2017 - vol. 8(Issue 3) pp:NaN1914-1914
Publication Date(Web):2016/11/01
DOI:10.1039/C6SC03038F
Two heavy atom-free luminophores (SHB2t and SDB2t) with simple molecular structures have been synthesized via Suzuki coupling reactions in which both display white-light emission with prompt fluorescence and room temperature phosphorescence (RTP) in the solid state. The impressive RTP of the luminophores is produced by a synergistic effect of the strong intermolecular hydrogen bonding in addition to the spin–orbit coupling of the sulfonyl oxygen atoms and the moderate singlet-triplet energy gaps (ΔEST). These factors facilitate the intersystem crossing (ISC) process to generate triplet excitons in which the molecular conformations become immobilized to effectively suppress radiationless decay. Under the stimuli of mechanical force and solvent vapor, the RTP of SHB2t and SDB2t can be simply turned off and on by breaking and reforming the robust hydrogen bonding, which leads to remarkable and reversible mechanochromism between white and deep-blue emission. Moreover, two different thermochromic processes have been observed for the pristine and ground samples of SDB2t, in which a tricolor switching system between white, deep-blue and blue emission has been successfully achieved through the sequential control of grinding, heating and fuming. From detailed studies we have determined that the mechanism for the thermochromism of SDB2t is correlated with the rearrangement of the white-light emitting molecules to a new packing mode without RTP emission.
Co-reporter:Xiqi Zhang, Zhenguo Chi, Bingjia Xu, Chengjian Chen, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Journal of Materials Chemistry A 2012 - vol. 22(Issue 35) pp:NaN18513-18513
Publication Date(Web):2012/07/20
DOI:10.1039/C2JM33140C
Distyrylanthracene derivatives, AnP3 and AnP3P with triphenylethylene end-groups, and AnP4 and AnP4P with tetraphenylethylene end-groups, were synthesized and characterized using nuclear magnetic resonance, mass spectrometry, elemental analysis, photoluminescence, ultraviolet-visible absorption, wide-angle X-ray diffraction, differential scanning calorimetry and other techniques. The results show that the piezofluorochromic properties of these four aggregation-induced enhanced emission (AIEE) compounds were influenced significantly by the structures of the end-groups in the molecules. The AnP4 and AnP4P derivatives with tetraphenylethylene end-groups exhibited distinct piezofluorochromic properties, which might be switched reversibly upon pressing or annealing because of crystalline-amorphous phase transformation. Thus, we propose that those AIEE compounds that contain steric hindrance groups may exhibit evident piezofluorochromic activities.
Co-reporter:Xiaofang Li, Xiqi Zhang, Zhenguo Chi, Xiaojuan Chao, Xie Zhou, Yi Zhang, Siwei Liu and Jiarui Xu
Analytical Methods (2009-Present) 2012 - vol. 4(Issue 10) pp:NaN3343-3343
Publication Date(Web):2012/08/16
DOI:10.1039/C2AY25564B
A novel probe incorporating tetraphenylethylene and benzoquinone into a molecule was synthesized and studied for the selective detection of biothiols. The probe was found to have a highly selective response to biothiols through a thiol–ene click-reaction with fluorescence turn-on feature. The observable color changes before and after biothiol addition indicated that the probe was suitable for naked-eye biothiol detection.
Co-reporter:Zhiyong Yang, Zhu Mao, Zongliang Xie, Yi Zhang, Siwei Liu, Juan Zhao, Jiarui Xu, Zhenguo Chi and Matthew P. Aldred
Chemical Society Reviews 2017 - vol. 46(Issue 3) pp:NaN1016-1016
Publication Date(Web):2017/01/24
DOI:10.1039/C6CS00368K
Organic materials that exhibit thermally activated delayed fluorescence (TADF) are an attractive class of functional materials that have witnessed a booming development in recent years. Since Adachi et al. reported high-performance TADF-OLED devices in 2012, there have been many reports regarding the design and synthesis of new TADF luminogens, which have various molecular structures and are used for different applications. In this review, we summarize and discuss the latest progress concerning this rapidly developing research field, in which the majority of the reported TADF systems are discussed, along with their derived structure–property relationships, TADF mechanisms and applications. We hope that such a review provides a clear outlook of these novel functional materials for a broad range of scientists within different disciplinary areas and attracts more researchers to devote themselves to this interesting research field.
Co-reporter:Tao Yu, Depei Ou, Zhiyong Yang, Qiuyi Huang, Zhu Mao, Junru Chen, Yi Zhang, Siwei Liu, Jiarui Xu, Martin R. Bryce and Zhenguo Chi
Chemical Science (2010-Present) 2017 - vol. 8(Issue 2) pp:NaN1168-1168
Publication Date(Web):2016/09/02
DOI:10.1039/C6SC03177C
This study probes the effect of intramolecular rotations on aggregation-induced emission (AIE) and leads to a kind of supramolecular mechanoluminescent material. Two hydrogen-bonded organic frameworks (HOFs), namely HOFTPE3N and HOFTPE4N, have been constructed from nitro-substituted tetraphenylethene (TPE) building blocks, namely tris(4-nitrophenyl)phenylethene (TPE3N) and tetrakis(4-nitrophenyl)ethene (TPE4N). Using single-crystal X-ray diffraction analysis, two types of pores are observed in the HOFTPE4N supramolecular structure. The pore sizes are 5.855 Å × 5.855 Å (α pores) and 7.218 Å × 7.218 Å (β pores). Powder X-ray diffraction and differential scanning calorimetry studies further reveal that the α pores, which contain nitrophenyl rings, quench the emission of HOFTPE4N. This emission can be turned on by breaking the α pores in the HOFs by grinding the sample. Temperature-dependent emission studies demonstrate that the emission quenching of HOFTPE4N is attributed to the intramolecular rotations of nitro-substituted phenyl units within the space of the α pores. These results clearly reveal AIE by controlling the intramolecular rotations, which can serve as a basis for developing mechanoluminescent materials.
Co-reporter:Zhiyong Yang, Zhu Mao, Zongliang Xie, Yi Zhang, Siwei Liu, Juan Zhao, Jiarui Xu, Zhenguo Chi and Matthew P. Aldred
Chemical Society Reviews 2017 - vol. 46(Issue 3) pp:NaN1016-1016
Publication Date(Web):2017/01/24
DOI:10.1039/C6CS00368K
Organic materials that exhibit thermally activated delayed fluorescence (TADF) are an attractive class of functional materials that have witnessed a booming development in recent years. Since Adachi et al. reported high-performance TADF-OLED devices in 2012, there have been many reports regarding the design and synthesis of new TADF luminogens, which have various molecular structures and are used for different applications. In this review, we summarize and discuss the latest progress concerning this rapidly developing research field, in which the majority of the reported TADF systems are discussed, along with their derived structure–property relationships, TADF mechanisms and applications. We hope that such a review provides a clear outlook of these novel functional materials for a broad range of scientists within different disciplinary areas and attracts more researchers to devote themselves to this interesting research field.
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